Gabriel Likes Pranks
by Intentions
Summary: It's true- Gabriel used to be referred to as the Trickster, and there's a reason. However, this prank may work in the favor of Castiel...
1. The Trials

Castiel looked down at the crumpled piece of paper in his hand.

"Why do I have to do this again? You weren't very forth coming with details." Castiel looked up dubiously at Gabriel who was leaning against the wall and smiling. If he was being honest, it was kinda freaking Castiel out.

"Oh, Cass," Gabriel said with amusement in his voice. "Just play my game, Brother. I told you that I need your help." He flashed a grin.

"I don't see how playing a 'game' assists you in any way." Castiel stared at Gabriel with concern; not concern for his devious brother, but for the result of these so-called trials Gabriel assigned Castiel with.

"Oh, trust me," Gabriel flashed Cass a mega-watt smile. "It helps me more than you could know." Gabriel pushes off of the wall and walks towards Cass. "Just do it. Please?"

That puzzled Cass, his big brother rarely asked for help, and certainly didn't use the word 'please'. So Castiel conceded and not to mention his interest was certainly piqued at this point.

* * *

><p><em>Hello, my lovelies. I hope you are intrigued by the premise of this fanfiction. Cass will go through 3 trials, all involving Dean. I would like to give credit to my friend, Destiel4shnurps, who helped me write this.<em>


	2. Trial 1

Castiel eyed Dean, nervous. His first trial wasn't very settling. Dean was sitting on a motel bed, flipping impatiently through an old-looking book.

"Dammit," Dean grumbled with a scowl. "How does Sam read these things?" This was Castiel's chance; Dean would be caught off guard for his first trial.

Castiel loosened his tie and undid the top button on his shirt. He walked slowly towards Dean who was paying him no mind. It was beginning to frustrate him. He decided to be a bit more bold. He cleared his throat and then got onto the bed with Dean. He was on his knees at the foot of the bed and suddenly he felt extremely vulnerable. His cheeks flamed pink and he peeked at Dean through his lashes.

Dean looked at the blushing angel, his eyebrows knit together. "Uh, what's up, Cass?" He asked. Cass looked away quickly.

"Uh… um…" Castiel stuttered. "Y-you look very… very nice, Dean." He glanced back over at Dean who's eyebrows rose.

"Oh, well… Thank you Cass." Dean cleared his throat and looked back to his book, attempting to keep his composure. "So you gonna help me figure out how to gank the evily-goodness that is this mega-rugaru or what?" Castiel's eyes widened.

"I assure you there is no goodness in a rugaru," he said intently. The angel remembered the trial he was supposed to do then shook his head. "I mean, Dean, you don't just look nice. You look _very_ nice." Recalling the instructions of the first trial, he whistled a single note, and once Dean looked up at him with alarm, he winked awkwardly. Dean's mouth opened slightly, staring at Castiel with bewilderment.

"I… you…" Dean was very flustered.

"I must be going now," the angel said, standing.

_Trial One: Compliment Dean's appearance, whistle at him, and wink._

Trial One complete.


	3. Trial 2

It had been a couple days since the first trial, and Cass was dreading the second. The first trial wasn't that bad now that Castiel looked back on it. He could probably do it again but the second trial was nothing like the first. It would be more difficult and much more awkward than the first.

"I don't know if I can do this." Castiel mumbled to no one in particular.

Cass appeared in front of Dean and immediately felt a confusing array of emotions and feelings. Cass knew that this is what would be happening, he just hadn't exactly expected _this_. Dean was naked on the bed and a sheen of sweat covered his skin and made him seem to glow. Castiel felt the urge to look away but also he wanted to do to Dean what Dean was doing to himself.

Dean was unaware of Cass and continued to thrust helplessly into his hand moaning and writhing. Cass's cheeks flamed and he wanted nothing more then to go to Dean and touch him. He felt his body respond to the sight and his pants became tighter.

"Fuck! Ah Cass!" Dean bit his soft lower lip and continued pleasuring himself. Cass gasped at the feeling that rushed straight to his groin when Dean moaned his name.

"Dean." Cass's voice was huskier than normal and he instinctively palmed himself through his pants. Dean looked up panicked but he didn't stop. Suddenly he arched his back and screamed out. "Oh Cass!" Thick spurts of hot white liquid covered Dean's hand and stomach. He was suddenly aware of Cass.

"You're beautiful." Cass whispered, awestruck, and with a flutter of wings he was gone.

Cass was now in the middle of a dark and cool field, horny and not sure what to do about it.

_Trial Two: Watch Dean jerk off until he comes. _

Trial Two complete.


	4. Trial 3

Dean sat on his bed, alone. Thank God Sammy wasn't there to see his sweaty, panting brother. Dean hadn't cleaned himself up yet and remained sitting, head in his sticky sticky hands. "What was Cass doing… standing there just… staring at me?" Dean asked aloud, raising his head to look up at the ceiling.

"It was part of his second trial."

Dean looked up in alarm, covering his naked body, to see Gabriel leaning against the motel door with a smirk on his face. "What the hell, dude?!"

"Castiel's trials are going quite beautifully, if I say so myself." The mischievous angel walked towards Dean like a predator, a purr escaping his throat. "Although, I think I'll finish the third trial and dismiss Cass from his job."

Dean clutched a blanket against his sweaty, naked body, nervous. "W-what trials?…" Gabriel sat on the bed with Dean and caressed his face, sending a shiver down Dean's spine. All of a sudden, Castiel poofed into the room.

"Don't worry, Deanie-weanie," Super-Cass said (while wearing a cape). "I'll save your virginity." Precious Deanie's eyes twinkled like falling angels in the night sky.

"My hero," he squeaked. Castiel tickled Gabriel and he became naked. Both of them.

"Leave my Deanie alone," Cass screamed. Gabriel became scared and pooped away. Cass turned and looked at Dean. Dean's breath hitched in the back of his throat because of the intense stare Cass gave him. Castiel pounced on Dean, pinning him to the bed.

"It's time to finish my third trial," he purred. Dean looked into Castiel's eyes as the angel slowly lowered his face to Dean's. There was a long silence.

"April Fools."

"W-what?…"

The lights flicked on, and there stood Gabriel and Sammy, laughing their asses off as confetti fell from the ceiling. Castiel jumped away and joined in on Gabriel and Sam's laughter as Dean, ashamed, covered his mother-fucking huge erection.

"S-so," Dean whispered. "Do you have any feelings for me at all?"

Castiel looked at Dean with a blank stare.

"What the fuck are you talking about?"


End file.
